David Ramirez
Pending
$950,000$975,0004 bd3 ba3,516 sqft$270 /sqft$6,376 /mo all-in ↓

1002 OAKDALE STREET, WINDERMERE, FL, 34786

Pending110 days on marketListed Apr 14, 2026MLS #TB8495717

Reduced $25KSingle Family ResidenceWINDERMERE TOWN

About this home

1002 OAKDALE STREET

Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is open to negotiating a closing cost credit, providing added flexibility and value for buyers for closing costs or rate buy down. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.

Facts & features

The home at a glance

4

Bedrooms

3

Bathrooms

3,516

Sqft

0.29 ac

Lot size

4

Garage

1973

Year built

One

Levels

$270

Per sqft

Fireplace

Inside

FlooringCarpet · Engineered Hardwood · Tile
AppliancesDishwasher · Microwave · Range · Refrigerator
InteriorThermostat · Walk-In Closet(s)
LaundryInside
CoolingCentral Air
HeatingElectric

Outside & construction

RoofShingle
ConstructionStucco
FoundationSlab
FacesSouthwest
ExteriorBalcony

Community & fees

Taxes (2025)$8,799/yr

Utilities & systems

UtilitiesPublic
WaterPublic

The numbers

What it really costs

Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.

$6,376 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$5,126
PMI (est., until 20% equity)$356
Property tax — 2025 actual bill$733
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $95,000Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.

These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $95,000
Interest rate6.00%
Loan term

Estimated payment

$6,376/mo

Principal & interest$5,126
PMI (est., until 20% equity)$356
Property taxes (actual bill)$733
Est. insurance$160

Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.

Where it sits

Inside Windermere

Map of 1002 OAKDALE STREET

Drive times from this address

Universal Orlando14 min
Downtown Orlando23 min
Walt Disney World25 min
Orlando Int’l Airport (MCO)35 min

Estimated driving times, typical traffic. Data © OpenStreetMap contributors.

Get to know Windermere. See the full Windermere guide →

WINDERMERE 34786 — neighborhood snapshot

Population

43,700

Median age

37.9

Median income

$131,409

Median home value

$621,300

Avg household

2.9

Households w/ children

6,277

For the school run

Orange County School District

ElementaryWindermere Elementary★★★★★
HighOlympia High★★★★★
MiddleGotha Middle★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Windermere market

Seller’s marketBalanced5.5 months of inventoryBuyer’s market

$839K$1.0M

Windermere median sold, yr/yr

96.4%

Sale-to-list ratio (12 mo)

Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.

This home is listed 19% above the WINDERMERE 34786 median. See the full Windermere market guide →

Paper trail

This home's history

CurrentPrice reduced to $950,000 $25K
Apr 14, 2026Listed at $975,000 · 110 days on market since
1973Built · WINDERMERE TOWN

Your home team

The pros in your corner

Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

David Ramirez

Your agent

David Ramirez

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 1002 OAKDALE STREET — start here.

Andrew Acosta

Your lender

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Pre-approval, rates, and the real monthly number for 1002 OAKDALE STREET — before you fall in love.

See it in person

Schedule a tour

Pick a day that works — this goes straight to David's phone and CRM.

Goes straight to David’s phone and CRM.

Straight answers

1002 OAKDALE STREET FAQs

What would the monthly payment be for 1002 OAKDALE STREET?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,376/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.

What are the property taxes on 1002 OAKDALE STREET?+

The most recent tax bill on record (2025) was $8,799. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.

How does the price compare to other homes in Windermere?+

At $950,000, this home is listed about 14% below the Windermere median of $1,099,500. The market section on this page shows how the area is trending.

Which schools are assigned to 1002 OAKDALE STREET?+

Windermere Elementary (elementary), Olympia High (high), Gotha Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.

The brief

Four things that matter here

01Positioned at the premium end

$950,000 runs 19% above the WINDERMERE 34786 median.

02Time on market is leverage

110 days on market against a Windermere median of 32 — sellers in this position are usually ready to negotiate.

03Strong assigned schools

Windermere Elementary, Olympia High, Gotha Middle — Windermere Elementary rates 5 of 5. Always verify assignments with the district.

04The price has already moved

Listed at $975,000, now $950,000 — a $25K cut. The full history is in the market section below.

Listing courtesy of KELLER WILLIAMS SUBURBAN TAMPA · Frank Smith. MLS #TB8495717.

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.

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1002 OAKDALE STREET, WINDERMERE, FL — 4 Bed, 3 Bath — $950,000 | CENTURY 21 Edge